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Aryl boron derivative based thermally activated delayed fluorescent material and organic light-emitting device

A technology of thermal activation delay and derivatives, applied in luminescent materials, electro-solid devices, electrical components, etc., can solve the problems of weak rigidity, large non-radiative transition rate, and complex co-deposition preparation of luminescent layer.

Inactive Publication Date: 2018-02-16
FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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  • Abstract
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  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the weak rigidity of this type of molecules, the high non-radiative transition rate leads to low luminous efficiency.
At the same time, most of the existing phosphorescent materials and TADF materials have a significant concentration quenching effect, resulting in most of the existing high-efficiency OLED devices being doped devices
However, the selection of the host material and the co-deposition preparation of the light-emitting layer are relatively complicated in the preparation of doped devices.

Method used

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  • Aryl boron derivative based thermally activated delayed fluorescent material and organic light-emitting device
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  • Aryl boron derivative based thermally activated delayed fluorescent material and organic light-emitting device

Examples

Experimental program
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Effect test

Embodiment 1

[0059] Synthetic method of structural compound shown in formula I-1:

[0060]

[0061] 2-Bromo-3-fluorotoluene (1.89g, 10mmol), carbazole (1.67g, 10mmol) and cesium carbonate (6.52g, 20mmol) were added to 15mL dimethylformamide (DMF), and the mixture was stirred at 150°C After 12 hours, it was poured into 200ml of water, and the precipitate was collected by filtration. After column purification, a total of 3.1 g of white solid 9-(2-bromo-3-methylphenyl)carbazole was obtained, with a yield of 92%.

[0062] 9-(2-bromo-3-methylphenyl)carbazole (5mmol, 1.68g) was dissolved in 15mL of dry cyclopentyl methyl ether, and n-BuLi hexane solution (2.5 M, 2mL, 5mmol), and continued to stir at this temperature for 30 minutes, then added dropwise a solution (5mL) of bis(trimethylphenyl)boron fluoride (1.34g, 5mmol) in cyclopentyl methyl ether, dropwise Upon completion the mixture was warmed to room temperature and stirred overnight. After completion of the reaction, add saturated aque...

Embodiment 2

[0066] Synthesis method of the structural compound shown in formula I-2: the reactant carbazole is replaced by 3,6-di-tert-butyl carbazole, and through the same synthesis method as in Example 1, the structural compound shown in formula I-2 is obtained, and the total product rate of 61%.

[0067] The molecular weight obtained by mass spectrometry: 617.42

[0068] The relative molecular mass percentages of each element (C / H / N) obtained by elemental analysis: C, 87.63; H, 8.45; N, 2.22.

Embodiment 3

[0070]Synthesis method of the structural compound shown in formula I-3: the reactant carbazole is replaced by 9,10-dihydro-9,9-dimethylacridine, and the compound of formula I-3 is obtained through the same synthesis method as in Example 1 The structure compound is shown, and the total yield is 57%.

[0071] The molecular weight obtained by mass spectrometry: 547.34

[0072] The relative molecular mass percentages of each element (C / H / N) obtained by elemental analysis: C, 87.78; H, 7.75; N, 2.50.

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Abstract

The invention relates to an aryl boron derivative based thermally activated delayed fluorescent material and an organic light-emitting device. The thermally activated delayed fluorescent material hasa structure shown as formula A. The invention also relates to an organic light-emitting device, which consists of a luminescent layer, and the luminescent dye in the luminescent layer is the thermallyactivated delayed fluorescent material. The thermally activated delayed fluorescent material has very small single state-triplet state energy gap, and at room temperature, triplet state exciton can be upconverted to triplet state excitonic luminescence by thermal activation. The thermally activated delayed fluorescent material has the advantages of simple synthesis, high luminous efficiency, small concentration quenching effect and good solubility. And the organic light-emitting device based on the material can acquire high efficiency and good device stability.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials and devices, in particular to a thermally activated delayed fluorescent material and organic electroluminescent devices based on aryl boron derivatives. Background technique [0002] Organic light emitting diode (OLED) technology has attracted much attention due to its great application potential in the fields of display and lighting. Among them, the development of luminescent materials is the core of OLED technology and the focus of industry competition. According to spin statistics, the ratio of singlet excitons to triplet excitons generated by the recombination of holes and electrons in the light-emitting material is 1:3. It is generally believed that traditional fluorescent materials can only use singlet excitons to emit light, and the highest theoretical internal quantum efficiency of the device is 25%. Phosphorescent materials based on platinum heavy metal complexes have...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/54C09B57/00
CPCC09K11/06C07F5/027C09B57/00C09K2211/1007C09K2211/1014C09K2211/1029H10K85/6572H10K50/11
Inventor 卢灿忠陈旭林贾吉慧
Owner FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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